Like punk rock and gangsta rap after it, outlaw country is part of an old, sometimes lucrative American tradition of celebrating defiance in song. Michael Streissguth’s engaging cultural history of outlaw country reminds us of the artistry that went into marketing triumphs such as “Wanted! The Outlaws,” a 1976 compilation album that looked like a bullet-riddled, Old West-era, dead-or-alive poster and became country music’s first certified million-selling LP.

A professor at Le Moyne College, Streiss­guth has previously written books and made two documentaries about Johnny Cash, whose influence on Waylon Jennings, Willie Nelson and Kris Kristofferson soon becomes apparent in this account. Through his prison concerts and the national TV show he broadcast from the Grand Ole Opry’s Ryman Auditorium, Cash demonstrated how to move between the Nashville establishment and the rest of the world while living by his own rules. After various other combined efforts, Cash, Jennings, Nelson and Kristofferson came together as the Highwaymen in 1985 — a moniker suggesting considerable touring time as well as a certain amount of criminality.

Streissguth’s focus, though, is on the years between 1965 and 1975, when a group of individuals and shifting societal currents managed to change how Nashville operated. This story’s central three renegades were all from Texas but arrived at country music’s capital from different angles. Born in Brownsville, Kristofferson was a high school football star in California and a Rhodes scholar before joining the Army. He came to Nashville with a head full of stories and lyrics, and he raised extra cash by flying helicopters to Gulf of Mexico oil rigs. By 1965, Nelson — from central Texas — had gained acclaim for his stellar songwriting (“Crazy,” “Night Life,” “Funny How Time Slips Away”) and live performances, but as a recording artist he suffered from uninspiring production and insufficient promotion. Hailing from West Texas, Jennings had developed “a restless union of country and rock” after playing in Buddy Holly’s road band, but he also struggled against the assembly-line strictures of the Nashville Sound.

All three simply wanted to make the music they heard in their heads, and Streissguth pinpoints their great gifts along with their frustrations when Nashville’s decision-makers wouldn’t get out of their way. Kristofferson’s rambling ballads featured “smart turns of phrase and knowing maturity” that helped inspire the 1970s singer-songwriter phenomenon. The “PG overtones of his songs” were somewhat shocking at the time, but Streissguth notes that they “echo still in today’s country music.” Jennings combined a “rough baritone” with songwriting chops and a percussive live show, and Nelson’s “hard Texas twang . . . danced and flirted with the rhythm,” but it wasn’t until they won the right to record with producers and musicians of their choosing that they achieved commercial and artistic success simultaneously.

Alongside these musical evolutions, Streissguth tells of Nashville’s transformation from a clean-cut and segregated city in the ’50s into a dynamic, somewhat dilapidated cultural capital in the mid-’70s, one worthy of movie director Robert Altman’s sharp, satirical eye. In addition to depicting country music’s hierarchies, Altman’s “Nashville” showed how the freewheeling ethos of the ’60s had made its way into corners of the city. Glaser Sound Studios (dubbed Hillbilly Central) and clubs like Exit/In fostered uninhibited collaboration. As songwriter Mickey Newbury remarked back then, “Nashville’s a great place to be right now — like Paris in the twenties — a place where you can get together with people and rap.” Alert to other perspectives, Streissguth starts the next chapter with Kinky Friedman’s terse rebuttal: “Paris of the thirties, my ass. It was one big con.” (And, yes, the ’20s and ’30s must have blended together by the 1970s.)

Friedman was no doubt fonder of Austin, which had live-music venues that Streissguth paints as cross-cultural hotbeds, their bellowing crowds made up of hippies, cowboys, truck drivers and state office workers. Nelson found a new home there as well as a new look. He “often wore a cowboy hat, and with every passing week . . . his hair dropped lower and the whiskers on his face multiplied. . . . He had gone from looking like a singing insurance peddler to the spiritual leader of a back to nature pod.”

The book offers a wealth of characters (including a couple of actual outlaws) and memorable moments, as when Richard Nixon christened the Opry House in March 1974. The president apparently found the occasion a respite from Washington’s relentless Watergate scandal-mongering: “Politicians in the front rows cheered him, fans pressed the stage as if he were Hank Williams come back, and wide-eyed cast members lingered in the wings watching his every move.” Two years later, the tide turned toward the Democrats as Jimmy Carter recruited a long list of longhaired musicians to his campaign. Streissguth repeats the legend that Nelson once visited Carter and lit up a joint on the White House roof.

Though Kristofferson has been an impressive songwriter and actor, the often-raucous Jennings and the shaman-hippie-cowboy Nelson get most of Streissguth’s attention. He details how they made such outlaw-country milestones as Jennings’s album “Honky Tonk Heroes” (1973) and Nelson’s spare, entrancing “Red Headed Stranger (1975), which Streissguth calls his “first true concept album.” The pair also formed the center of “Wanted!,” (1976), which also featured Jennings’s wife, Jessi Colter, and Tompall Glaser, a less-known maverick who died in August of this year.

A longtime pinball and pill addict, Jennings provides the book with more than his share of outrageous stories and apt song titles (“Don’t You Think This Outlaw Bit’s Done Got Outta Hand?”). He died, apparently clean and sober, from diabetes-related health problems in 2002. Nelson, on the other hand, has survived to become an American icon, seemingly always on the road again, “onstage with a smile and a gut string.”

The only off-key note the book strikes is its conclusion — a heartwarming visit Jennings made to a critically ill fan in 1980. After hanging out with the man and his family, Jennings and the band got on their bus and “rolled south to their next show.” The stricken man died seven hours later. The anecdote reveals a lesser-known side of Jennings, but it marks an abrupt end to both the fan and an otherwise fascinating chronicle.

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Comments our editors find particularly useful or relevant are displayed in Top Comments, as are comments by users with these badges: . Replies to those posts appear here, as well as posts by staff writers.